WO2023023815A1 - Highly loaded fludioxonil formulations - Google Patents

Highly loaded fludioxonil formulations Download PDF

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Publication number
WO2023023815A1
WO2023023815A1 PCT/AU2022/051043 AU2022051043W WO2023023815A1 WO 2023023815 A1 WO2023023815 A1 WO 2023023815A1 AU 2022051043 W AU2022051043 W AU 2022051043W WO 2023023815 A1 WO2023023815 A1 WO 2023023815A1
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Prior art keywords
fludioxonil
spp
formulation
fungicide
fungicides
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PCT/AU2022/051043
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French (fr)
Inventor
Andrew HORSFIELD
Peter Vaughan
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Adama Australia Pty Limited
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Priority to AU2022331939A priority Critical patent/AU2022331939A1/en
Publication of WO2023023815A1 publication Critical patent/WO2023023815A1/en

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A—HUMAN NECESSITIES
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    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
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    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/34—Nitriles
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    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/46—N-acyl derivatives
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    • A01N37/52—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing groups, e.g. carboxylic acid amidines
    • A—HUMAN NECESSITIES
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
    • A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
    • A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
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    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • A01N47/14—Di-thio analogues thereof
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    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
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    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
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Abstract

The invention provides a stable, highly loaded fludioxonil suspension concentration formulation with more than 250 g ai/L. In one embodiment, fludioxonil is the sole active ingredient. In field trials, the fludioxonil formulation has proved to be effective in controlling Yellow Sigatoka (Mycosphaerella musicola) in a banana crop and in controlling grey mould (Botrytis cinerea) in a grapevine. The invention also discloses synergistic combinations of fludioxonil with other fungicides.

Description

Highly Loaded Fludioxonil Formulations
Technical Field
The invention relates to fludioxonil formulations. In one aspect, the invention is concerned with a highly loaded solo fludioxonil SC formulation.
Background Art
Fludioxonil (4-(2,2-Difluorobenzo[d][l,3]dioxol-4-yl)-lH-pyrrole-3-carbonitrile) is a phenylpyrrole fungicide that inhibits a protein kinase involved in a regulatory step of cell metabolism in a range of fungi. Major use crops for fludioxonil include:
• Seed treatment for Fusarium, Microdochium, Rhizoctonia, Tilletia, Pyrenophora and Septoria in cereals and non-cereal crops;
• Foliar use as a solo or in mixtures in vegetables, ornamentals, tree crops, grapes for Botrytis, Monilinia, Sclerotinia and Alternaria;
• Turf use on Fusarium, Helminthosporium, Rhizoctonia, Sclerotinia; and
• Post-harvest control of Botrytis, Monilinia and Penicillium.
Previously, fludioxonil liquid formulations were typically 250 g ai/L limited to a maximum active ingredient loading of about 250 g ai/L. Surprisingly, aside from formulations used to treat seeds prior to drying and bagging them, significantly higher loadings had not been previously developed and most suspension concentrate (SC) formulations available are either in mixtures with other active ingredients or used for post-harvest treatment of fruit.
Highly loaded formulations are desirable. The benefits of high concentration formulations can be observed through the entire supply chain, including:
• Less volume of raw materials to procure;
• Fewer litres or kilograms to formulate;
• Fewer drums, labels and caps required for the same quantity of active ingredient;
• Less freight and storage from procurement of raw materials through to the end user;
• Less volume for the end user to handle during mixing and application;
• Fewer drums to dispose of post application; and More cost-effective formulations for the manufacturer.
Any improvement in the delivery of the active ingredient from synthesis through to the point of application can enhance the efficiency and improve profitability of the agricultural chemical industry.
There is also a need to provide a highly loaded fludioxonil suspension concentration formulation which has fludioxonil as the only active ingredient, to provide more options for tank mixing with compatible products.
Additionally, novel and synergistic mixtures with fludioxonil can also provide benefits for disease control and plant protection, yield and quality. Mixtures of selected fungicides have several advantages over the use of a single fungicide including (a) an increase in the spectrum of diseases controlled or an extension of control over a longer period of time, and (b) a delay in the appearance of resistant fungal species to selected fungicides.
Fludioxonil is widely used in grapes for the control of Botrytis bunch rot (Botrytis cinerea). The most widely used formulation sold globally is a mixture of cyprodinil and fludioxonil ("Switch®"). This coformulation is used during flowering and post-flowering for Botrytis bunch rot in both wine grape and table grape production. In wine grape production, residues in wine may not be acceptable in some export markets. In Australia, Switch® can now only be applied once per season due to cyprodinil residues in wine. Under the current situation where fludioxonil is applied as a coformulation with cyprodinil, fludioxonil can only be applied once per season in export wine grapes even though it is not readily detected in wine after two applications.
Reference to any prior art in the specification is not an acknowledgment or suggestion that this prior art forms part of the common general knowledge in any jurisdiction or that this prior art could reasonably be understood, regarded as relevant, and/or combined with other pieces of prior art by a skilled person in the art.
Summary of the Invention
A new stable, highly loaded fludioxonil suspension concentration formulation with more than 250 g ai/L has been developed. This liquid formulation has a higher concentration than existing fludioxonil SC formulations. In one embodiment, the loading of fludioxonil is about 500 g/L.
The formulation of the invention may include excipients such as one or more of a dispersant, a wetting agent, a stabiliser, a humectant, a rheology modifier, a preservative and an antifoaming agent. Water may be included.
In embodiments which include one or more of such excipients, the following are non-limiting examples:
• the dispersant is preferably an anionic dispersant, one example being Morwet® D-425;
• the wetting agent, which may also function as a stabiliser, is exemplified by Ethylan® NS- 500 LQ;
• the stabiliser may be a steric stabiliser, one example being Agrilan® 755;
• the humectant, which may also function as an anti-freeze agent, is exemplified by glycerine BP/EP/USP Grade;
• the rheology modifier is exemplified by Xanthum Gum TFST;
• the preservative is exemplified by Nipacide® BIT 20;
• the anti-foaming agent is exemplified by Gensil® 2000.
The formulation of the invention may have an aqueous content of, or less than, 60% w/v.
In one embodiment, the ratio of fludioxonil to total raw material (other than water) is equal to or more than about 5:1.
In one embodiment, the formulation of the invention is a solo formulation. It may be tank mixed with other fungicide modes of action, such as triazoles, strobilurins, phthalimides and others, to manage diseases of existing co-formulations with other fungicide modes of action with similar efficacy and crop safety. As a solo formulation, the formulation of the invention may be used in grapes and other berries for Botrytis, or in a tank mix or in rotation with fungicides having a different mode of action.
Embodiments of the solo formulation may be used in bananas for Mycosphaerella and other fungal leaf disease or in citrus as a foliar application e.g., for Alternaria, or other diseases. Alternatively, the formulation of the invention may be applied with a water-miscible oil and/or with at least one other fungicide having mode of action different from that of fludioxonil. Embodiments of the formulation may find foliar use in cereals crops as a solo application or in mixtures with other mode of action fungicides, e.g. triazoles, strobilurins, phthalimides, for control of foliar diseases such as Septaria tritici, Pyrenophora spp.
The majority of foliar uses for fludioxonil are in co-formulation with another fungicide, usually a translaminar or locally systemic active ingredient, such as cyprodinil or an SDHI (succinate dehydrogenase inhibitor). The ability to apply solo fludioxonil and achieve good control of a range of disease offers end users the ability to use fludioxonil in rotation with other fungicides having different modes of action compared to fludioxonil or in alternative tank mixtures and help manage fungicide resistance risk.
A new use for fludioxonil in crops such as canola has also been discovered: in-furrow application or early post-crop emergence as a solo can help reduce seedling infection. The infurrow efficacy and ability to enhance flutriafol are unexpected, as fludioxonil is not systemic and it has been only available pre-crop emergence as a seed treatment in canola. With flutriafol resistance increasing in blackleg (Leptosphaeria maculans), fludioxonil as an in-furrow application may reduce resistance selection pressure. Additionally, early foliar applications as either a solo or with a mode of action other than an SDHI will help reduce the selection pressure for blackleg resistance to SDHI seed treatments which have become widely used.
This new use is not confined to canola.
As used herein, except where the context requires otherwise, the term "comprise" and variations of the term, such as "comprising", "comprises and "comprised", are not intended to exclude further additives, components, integers or steps.
Further aspects of the present invention described in the preceding paragraphs will become apparent from the following description, given by way of embodiments and/or examples.
Synergistic Fungicidal Mixtures and Novel Application Sequences
According to one aspect, the present invention provides a synergistic fungicidal mixture comprising fludioxonil and at least one additional fungicide, plant activator or fertiliser.
According to another aspect, the present invention provides a composition comprising a mixture of fludioxonil and a de-methylation inhibitor fungicide, phthalimide fungicide and/or a strobiluron fungicide and at least one agriculturally acceptable carrier. Such compositions can be achieved either by tank mixing the fludioxonil solo with other fungicides or by coformulating fludioxonil with one or more additional fungicides and/or other components such as plant activators, adjuvants or fertilisers.
According to yet another aspect, the present invention provides a method of controlling fungal pathogens comprising applying to a locus of the disease a fungicidally effective amount of a mixture comprising fludioxonil, a de-methylation inhibitor, phthalimide and/or a strobilurin.
According to another aspect, the present invention provides a synergistic fungicidal mixture comprising fludioxonil and a de-methylation inhibitor fungicide, wherein the weight ratio between fludioxonil and the de-methylation inhibitor is between 1:10 and 10:1.
The present invention also provides a synergistic fungicidal mixture comprising fludioxonil and a phthalimide fungicide, wherein the weight ratio between fludioxonil and the phthalimide fungicide is between 1:50 and 10:1.
According to another aspect, the present invention provides a synergistic fungicidal mixture comprising fludioxonil and a strobilurin fungicide, wherein the weight ratio between fludioxonil and the strobilurin fungicide is between 1:50 and 10:1.
According to a further aspect the present invention provides a method of controlling fungal diseases by applying to a locus of the pathogen a fungicidally effective amount of a synergistic mixture of fludioxonil and at least one additional fungicide.
The present invention may provide a method of controlling diseases that have become resistant to fludioxonil and related fungicides. The combination of fludioxonil and other fungicides can provide greater fungicidal activity on pathogens that have become fungicide resistant such as, but not limited to, Botrytis cinerea, compared with the solo components.
The present compositions may include additional crop protection agents, for example pesticides, safeners, or agents for controlling insects or weeds. However, for the avoidance of doubt it is understood that such additional crop protection agents are unnecessary to achieve the synergistic effects of the present combinations.
In an embodiment, the mixture is applied on crops which include one or more of cereals, wheat, winter wheat, spring wheat, barley, winter barley, spring barley, triticale, cereal rye, fodder cereals, rice, canola, oilseed rape, maize, cotton, bananas, grapevines, pome fruit, stone fruit, almonds, macadamias, mangoes, strawberries and other berry crops, coffee, chickpeas, green beans, lettuce, leafy vegetables, potatoes, Allium spp, field peas, lentils, lupins, peanuts, soybeans, sugarcane, sugarbeet, fodder beet, beet vegetables, sunflower, non-crop areas, turfgrass and grassland. That is, the locus of diseases may occur in one or more of these crops.
In yet another embodiment, the target diseases may include one or more of Botrytis spp, Sclerotinia spp, Alternaria spp, Mycosphaerella spp, Cercospora spp, Fusarium spp, Rhizoctonia spp, Zymoseptoria tritici, Rhizopus spp, Phakopsora pachyrhizi, Pyrenophora spp, Monilinia spp, Colletotrichum spp, Penicillium spp, Aspergillus spp, Puccinia spp, .
In an embodiment, the fungicidal mixture is applied to the locus of the disease in an amount, or at a rate of application, of from 0.01 to 100 liter/ha. In yet another embodiment, the fungicidal mixture is applied in an amount of from 0.1 to 10 liter/ha. In another embodiment, the fungicidal mixture is applied in an amount of from 0.1 to 1 liter/ha. In a specific embodiment, the mixture is applied to the locus of the disease in an amount of 0.1 liter/ha. In yet another specific embodiment, the mixture is applied in an amount of 0.25 liter/ha. In still another specific embodiment, the mixture is applied in an amount of 0.5 liter/ha. In still yet another specific embodiment, 20 the mixture is applied in an amount of 0.75 liter/ha. In a further specific embodiment, the mixture is applied in an amount of 2 liter/ha. In yet another specific embodiment, the mixture is applied in an amount of 1 liter/ha.
In another embodiment, the fungicidal mixture is applied to the locus of the disease in an amount of from 1 to 5000 g/ha. In a further embodiment, the fungicidal mixture is applied in an amount of from 100 to 1000 g/ha.
In another embodiment, the present invention provides a kit comprising the fungicidal mixture as described herein, or components thereof. Such kits may comprise, in addition to the aforementioned active components, one or more additional active and/or inactive ingredients, either within the provided fungicidal composition or separately. Certain kits comprise fludioxonil and the partner fungicide(s), and/or a combination thereof, each in a separate container, and each optionally combined with a carrier. In an embodiment, the kit comprises fludioxonil, a de-methylation inhibitor fungicide, a phthalimide fungicide and/or a strobilurin fungicide. According to another aspect, the present invention provides a method for controlling a fungal disease, including the steps of: as a first step in a sequence, applying a composition containing fludioxonil as an active ingredient, as well as a composition containing as an active ingredient a fungicide having a mode of action different from that of fludioxonil, to a crop or ground area intended for growing a crop; and as a last step in the sequence, applying to the crop or ground area intended for growing the crop a composition containing fludioxonil as an active ingredient without any fungicide having a mode of action different from that of fludioxonil.
In this aspect of the invention, there is an optional second step of applying a composition containing as an active ingredient a fungicide having a mode of action different from that of fludioxonil, but without fludioxonil. With such an option, the last step in the sequence is the third step.
For the first step and the optional second step, fludioxonil may be tank mixed or coformulated with the other mode of action fungicide or each fungicide may be applied separately.
Non-limiting examples of other mode of action fungicides are flutriafol, azoxystrobin, epoxiconazole and prothioconazole.
A synergistic effect exists wherever the action of a combination of active components is greater than the sum of the action of each of the components alone. Therefore, a synergistically effective amount (or an effective amount of a synergistic composition or combination) as discussed herein is an amount that exhibits greater pesticidal activity than the sum of the pesticidal activities of the individual components.
In the context of this description and claims, the term "synergy" and its derivative terms are as defined by Colby S. R. in an article entitled "Calculation of the synergistic and antagonistic responses of herbicide combinations" published in the journal Weeds, 1967, 15, p. 20-22, and incorporated herein by reference in its entirety. The action expected for a given combination of three active components can be calculated as follows:
E = X+ Y- (X * F/ 100)
Where X = effect in percent using active compound A at an application rate a;
Y = effect in percent using active compound B at an application rate b; and
E = expected effect (in %) of A + B at application rates a + b.
If the value calculated in this manner is higher than the value E calculated according to Colby, a synergistic effect is present. When the percentage of control observed for the combination is equal to the expected percentage, there is an additive effect and wherein the percentage of fungicidal control observed for the combination is lower than the expected percentage, there is an antagonistic effect.
Detailed Description of Preferred Embodiments
Reference will now be made in detail to certain embodiments of the invention. While the invention will be described in conjunction with the embodiments and/or examples, it will be understood that the intention is not to limit the invention to those embodiments/examples. On the contrary, the invention is intended to cover all alternatives, modifications, and equivalents, which may be included within the scope of the present invention.
One skilled in the art will recognize many methods and materials similar or equivalent to those described herein, which could be used in the practice of the present invention. The present invention is in no way limited to the methods and materials described. It will be understood that the invention disclosed and defined in this specification extends to all alternative combinations of two or more of the features mentioned or evident from the text. All of these different combinations constitute various alternative aspects of the invention.
For the purposes of interpreting this specification, terms used in the singular will also include the plural and vice versa.
Example 1: Highly Loaded Fludioxonil Formulation
By way of example, a highly loaded SC formulation containing a fludioxonil concentration of about 500 g/L was prepared, designated as AD-AU-1921. The components are as set out in Table 1: Table 1
Formulation composition of fludioxonil 500 g/L SC (AD-AU-1921)
Figure imgf000010_0001
The active ingredient, Fludioxonil TGAC 98.4 %, was supplied by Rudong Zhongyi Chemical Co., Ltd The Second Haibin Road, Coastal Economic Development Zone, Rudong, Jiangsu Province, P.R. China 226407
Details of the components are as set out in Table 2:
Table 2: Component Details
Figure imgf000010_0002
Figure imgf000011_0001
Method
AD-AU-1921 SC is formulated in a batch process. A description of the method of formulation of the product and the sequence of operations to be followed is described below:
1. Charge the water into a suitable vessel equipped with an "F Type" saw tooth dispersion blade mixer.
2. Commence mixing and add the Gensil® 2030.
3. Maintain mixing and add the Morwet® D-425.
4. Maintain mixing and add the Ethylan® NS 500 LQ.
5. Maintain mixing and gradually incorporate the Fludioxonil Technical.
6. Apply high shear dispersion mixing using a rotor/stator type homogeniser (eg Silverson).
7. Maintain high shear mixing until mixture is homogeneous and free from agglomerates.
8. Commence recirculation milling using a Dyno-Mill KD or similar bead mill. Maintain the mill temperature below 35 °C. Grind the mill base until a particle size D (v, 0.5) 2.0 - 4.0 microns and D (v, 0.9) < 8.0 micron is achieved as determined by CIPAC MT 187.
9. Transfer the mill base to another suitable vessel equipped with a propeller type stirrer.
10. Maintain agitation at all times.
11. Maintain mixing and add the Agrilan® 755.
12. Premix the Glycerine with Nipacide® BIT 20 and Xanthum Gum TFST in a separate vessel.
13. Add this premix slowly to the mill base and continue to agitate until the xanthum gum is completely hydrated and dispersed.
14. Examine the product according to the specification. Adjust with water as required. Formulation Stability
5000 mL of product AD-AU-1921 was formulated as above. 2 x 1000 mL samples were assigned to stability study and each was packaged in HDPE containers with screw cap closure (commercial packaging material). Labels were attached to the assigned specimens in preparation for ambient and elevated temperature storage.
The specimens remained in their containers and were stored in an air-conditioned facility at approximately 21 °C for the period prior to ambient temperature and elevated temperature storage.
On the day of initiation of the accelerated storage trial, each of the specimens in their unopened containers were weighed on a top pan balance (Mettler PJ3600 Delta Range: SNR J29589) to determine a starting weight (for use as a comparison with weights at the conclusion of the storage period).
The sample designated for elevated temperature storage (Accelerated Stability sample TAS1) was placed into a thermostatically controlled oven (VWR Mini Incubator: SNR 0811V1169), heated to 54 ± 2 °C, for a period of 14 days. At the end of this period, the sample was removed from the oven and placed into a desiccation chamber to allow cooling to ambience.
The remaining AD-AU-1921 SC formulation sample (Time Zero sample T01) was stored at air- conditioned ambient temperatures (~21 °C) in a locked cabinet for the duration of the elevated temperature storage period.
A sample of AD-AU-1921 SC was prepared for low temperature stability testing by placing 100 mL of the ambient storage stability formulation sample (T01) into a 100 mL ASTM D96 graduated centrifuge tube and storing it in a refrigerated cabinet (Esatto Model EBF93W: SNR 5G386) at a temperature of 0 °C ± 2 °C for a total of 7 days.
The results of testing performed on storage stability samples are shown in Table 3 (Time Zero Sample), Table 4 (Accelerated Stability Sample) and Table 5 (Cold Temperature Stability Sample). Table 3 Time Zero Sample
Figure imgf000013_0001
Table 4 Accelerated Stability Sample
Figure imgf000014_0001
Table 5 Cold Temperature Stability Sample
Figure imgf000014_0002
Description of Methods Used
Relevant test parameters for suspension concentrate (SC) formulations are given in Section 3.2, Table 25 of the APVMA Guidelines for the Generation of Storage Stability Data for Agricultural Chemical Products (Version 2, 22 July 2015). An outline summary of each method employed follows:
Appearance, Physical State & Colour
These tests are performed visually and are described in descriptive terms.
Odour
This test is performed organoleptically and involves the use of descriptive terms.
Density CIPAC MT 3.3.2
A portion of the sample is weighed into a density bottle and diluted with water containing an anti-foam agent, using vacuum, if necessary, to remove occluded air. The volume of sample taken is then found by making up to capacity with the anti-foam solution and weighing. pH CIPAC MT 75.3
The pH value of a 1% v/v dilution of the formulation is determined by means of a pH meter and electrode system.
Brookfield RV Viscosity CIPAC MT 192
The viscosity of the formulation is measured in a standard measuring system using a Brookfield RV Viscometer.
Pourability CIPAC MT 148
The suspension concentrate is allowed to stand for a definite time and the amount remaining in the container after a standardized pouring procedure is determined. The container is rinsed and the amount then remaining is determined.
Spontaneity of dispersion CIPAC MT 160
The method is broadly similar to that used to determine suspensibility (CIPAC MT 184), except that the preparation of the suspension of known concentration employs only one inversion and a 5 min standing time. The top 9/lOths are the drawn off and the remaining l/lCJth is then determined gravimetrically and the spontaneity of dispersion calculated. Suspensibility CIPAC MT 184
A suspension of known concentration in CIPAC Standard Water is prepared, placed in a prescribed measuring cylinder at a constant temperature, and allowed to remain undisturbed for a specific time (30 minutes). The top 9/10ths are then drawn off and the remaining l/lCJth is then assayed chemically and the suspensibility calculated.
Wet Sieve Test CIPAC MT 185
A sample of the formulation is dispersed in water and the suspension formed is transferred to a sieve and washed. The amount of the material retained on the sieve is determined by drying and weighing.
Particle Size Analysis by Laser Diffraction CIPAC MT 187
A representative sample of the formulation is dispersed in water, and then passed through the beam of a laser. The light scattered by the dispersed particles is measured by a multi-element detector. Numerical values relating to the scattering pattern are calculated using an appropriate optical model and mathematical procedure to yield a volumetric particle size distribution.
Persistent Foam CIPAC MT 47.2
The sample is diluted in a measuring cylinder of standard dimensions which is inverted 30 times and the amount of foam created and remaining after certain times is measured.
Cold Temperature Stability of Liquid Formulations CIPAC MT 39.3
A sample is maintained at 0 ± 2 °C for 7 days and the nature and quantity of any separated material retained following wet sieving through a 75 pm sieve is determined.
Active Constituent Content - QChem Laboratories Analytical Method QCM-195.01
Fludioxonil content is determined by reversed phase high performance liquid chromatography using UV detection and external standardisation.
Packaging Stability
A sample of the product AD-AU-1921 in a HDPE container was weighed and then maintained at o
54 C for a period of 14 days. Any loss or gain in weight was recorded and the container examined, recording observations of any significant interaction with the formulation. The result is in Table 6. Table 6. Packaging Stability
Figure imgf000017_0001
No observable degradation, deformation, discolouration or etching of the container or lid was evident after accelerated storage. No odour was detectable emanating from the seal. No appreciable weight difference was determined over the 14-day period for both ambient and 54 °C storage conditions.
The product AD-AU-1921 was tested for compatibility with a range of partner products. The results are in Table 7:
Table 7. Formulation compatibility for fludioxonil 500 g/L SC (AD-AU-1921) at 400 mL/ha
Figure imgf000017_0002
Figure imgf000018_0001
As shown above, the AD-AU-1921 formulation containing 500 g ai/L was tested for accelerated storage stability at 54°C for 14 days and at 0±2°C for 7 days and was found to be stable and compatible with a wide range of other crop protection products, Example 2: Field Trials
Field Trial 1
A trial was conducted in a banana cv. Cavendish; plantation in I nnisfail, Queensland to assess AD-AU-1921 for use in control of Yellow Sigatoka (Mycosphaerella musicola). AD-AU-1921 was evaluated at 200 g ai/ha and compared to registered fungicides including epoxiconazole, difenconazole and mancozeb. All treatments were tank-mixed with parafinic spray oil at 4075 g ai/ha. Treatments applied with a Solo backpack mister at a water rate of 300 L/ha and 6 applications were applied an average spray interval of 24 days. The trial study was arranged in a complete randomized block design with four replicates.
Results of the trial indicated that AD-AU-1921 provided equivalent control to standard products (Table 8) and excellent crop safety. Table 8. Efficacy of AD-AU-1921 on yellow sigatoka (Mycosphaerella musicola) in bananas. Innisfail, Queensland
Figure imgf000019_0001
Field Trial 2
AD-AU-1921 was evaluated for the control of grey mould (Botrytis cinerea) in grapevines cv. Chardonnay in Western Australia. Fungicides were applied three times: at 80% capfall, prebunch closure and veraison (onset of the ripening of the grapes). AD-AU-1921 was compared with Switch® at an equivalent fludioxonil rate and Solaris®. AD-AU-1921 and the other fungicide treatments significantly reduced both the incidence and severity of grey mould damage on bunches when compared to the untreated control. There was no significant difference between AD-AU-1921 and Switch®, despite the additional Botryticide (cyprodinil) being applied with Switch® (Table 9).
There were no visible signs of phytotoxicity or adverse growth effects on either leaves or bunches by any treatment in this trial.
Table 9. Efficacy of AD-AU-1921 on Botrytis in grapes. Pemberton, Western Australia
Figure imgf000019_0002
Field Trial 3
AD-AU-1921 was evaluated as an in-furrow application for the control of blackleg (Leptosphaeria maculans) in canola in South Australia. Fungicides were applied in-furrow at planting, including AD-AU-1921 applied solo at 50 g ai/ha, flutriafol at 200 g ai/ha and AD-AU- 1921 + flutriafol.
AD-AU-1921 significantly reduced the severity of blackleg seedling infection (Table 10). While flutriafol applied solo was more effective than AD-AU-1921, the combination of AD-AU-1921 and flutriafol had the lowest level of blackleg infection.
In fact, the mixture of AD-AU-1921 with flutriafol exhibited synergy in control of blackleg seedling infection.
There were no visible signs of phytotoxicity or adverse growth effects in this trial.
Table 10. Efficacy of AD-AU-1921 on blackleg in canola. Salter Springs, South Australia
Figure imgf000020_0001
DAA = days after application
Bold indicates synergistic response (Colby)
Field Trial 4
AD-AU-1921 was evaluated for the control of grey mould (Botrytis cinerea) in grapevines cv. Chardonnay in Western Australia. Fungicides were applied three times: at 80% capfall, berries 4 mm diameter and berries 7 mm diameter. AD-AU-1921 and Solaris® were applied solo and in a tank mix at the first two timings and compared with AD-AU-1921 and Solaris® applied in a tank mix at 80% capfall followed by alternation.
The effect of fungicides was evaluated on berry splitting 32 days before harvest and Botrytis bunch incidence at harvest. The sequence of AD-AU-1921 and Solaris® applied in a tank mix then alternation was the most effective treatment (Table 11). The application of fludioxonil in a sequence with another mode of action was more effective than applying the two fungicides in a tank mix sequence. The application of fludioxonil solo also enables later use in export winegrapes where importing countries require no residues detected at the limit of detection.
There were no visible signs of phytotoxicity or adverse growth effects on either leaves or bunches by any treatment in this trial.
Table 11. Efficacy of AD-AU-1921 on Botrytis in grapes. Pemberton, Western Australia
Figure imgf000021_0001
1 Timings: A = 80% capfall; B = 4 mm berries; C = 7 mm berries DBH = days before harvest
Field Trial 5
A trial was conducted in couch turfgrass cv. Tiff at St Lucia, Queensland to assess AD-AU-1921 on dollar spot (Sclerotina homeocarpa). AD-AU-1921 and the standard fludioxonil solo (Medallion) were applied at 375 g ai/ha. All treatments were applied once using a hand boom and at a water rate of 490 L/ha. The trial study was arranged in a complete randomized block design with four replicates. Results of the trial indicated that AD-AU-1921 provided equivalent control to Medallion (Table 12) and excellent safety to couch turfgrass. To achieve the same dose rate and similar control, AD-AU-1921 was applied at 750 mL/ha compared with 3000 mL when applied at Medallion due to its low concentration of 125 g a i/L. Table 12. Efficacy of AD-AU-1921 on dollar spot (Sclerotinia homeocarpa) in couch turfgrass. St Lucia, Queensland
Figure imgf000022_0001
Field Trial 6
A trial was conducted in mandarin cv. Daisy at Gayndah, Queensland to assess AD-AU-1921 on emperor brown spot (Alternaria alternata). AD-AU-1921 and the registered standard fungicide
Amistar® (azoxystrobin 250 SC) were applied twice as a dilute application at BBCH 31. Crop safety and disease control were assessed after the first and second applications. The trial study was arranged in a complete randomized block design with four replicates.
Results of the trial indicated that AD-AU-1921 provided similar or superior control compared to both rates of Amistar® (Table 13) and excellent safety to mandarins.
Table 13. Efficacy of AD-AU-1921 on emperor brown spot (Alternaria alternata) leaf infection in mandarin cv. Daisy. Gayndah, Queensland
Figure imgf000022_0002
AUDPC = area under disease progress curve Field Trial 7
AD-AU-1921 was evaluated as a foliar application for the control of white mould (Sclerotinia sclerotiorum) in green beans cv. Stanley at Sassafras, Tasmania. AD-AU-1921 and Mirador® 625 were applied solo and in a tank mix and compared with the standard fungicide, Switch®. Fungicides were applied three times as a foliar spray at BBCH 61-62, 67-69 and 77 using a hand boom and an application volume of 300 L/ha.
Assessment of white mould incidence and severity indicated that AD-AU-1921 provided similar control compared to Switch® and superior control to Mirador® 625 (Table 14). The combination of AD-AU-1921 and Mirador® 625 was the most effective treatment in the trial. In fact, the mixture of AD-AU-1921 with Mirador® 625 exhibited synergy in control of white mould.
There were no visible signs of phytotoxicity or adverse growth effects in this trial.
Table 14. Efficacy of AD-AU-1921 on white mould (Sclerotinia sclerotiorum) in green beans cv. Stanley 18 days after application three. Sassafras, Tasmania
Figure imgf000023_0001
DAA = days after application
Bold indicates synergistic response (Colby)
Field Trial 8
A trial was conducted in mango cv. Parvin at Childers, Queensland to assess AD-AU-1921 on anthacnose (Colletotrichum gloeosporioides). AD-AU-1921 and registered standard fungicides including Dithane® Rainshield® and Octave® + Dithane® Rainshield® were applied three times as dilute applications at BBCH 61, 65 and 72. Crop safety and disease control were assessed after the final application. The trial study was arranged in a complete randomized block design with four replicates.
Results of the trial indicated that AD-AU-1921 provided superior control compared to Dithane® Rainshield® and similar control to Octave® + Dithane® Rainshield® (Table 15) and excellent safety to mangoes.
Table 15. Efficacy of AD-AU-1921 on anthracnose (Colletotrichum gloeosporioides) in mango cv. Parvin. Childers, Queensland
Figure imgf000024_0001
Field Trial 9 AD-AU-1921 was evaluated as a foliar application for the control of stripe rust (Puccinia striiformis f.sp. tritici) in wheat cv. Trojan at Bannockburn, Victoria. AD-AU-1921 and Soprano® 500 were applied solo and in a tank mix. Fungicides were applied twice times as a foliar spray at BBCH 33 and 39-41 using a hand boom and an application volume of 125 L/ha.
Assessment of stripe rust severity eight days after the second application indicated that AD-AU- 1921 provided a reduction in infection on all three top leaves. On the flag-1 and flag-2 the combination of AD-AU-1921 and Soprano® 500 was the most effective treatment (Table 16).
There were no visible signs of phytotoxicity or adverse growth effects in this trial.
Table 16. Efficacy of AD-AU-1921 on stripe rust (Puccinia striiformis f.sp. tritici) in wheat cv. Trojan after two fungicide applications. Bannockburn, Victoria
Figure imgf000024_0002
Figure imgf000025_0001
DAA = days after application
Field Trial 10
AD-AU-1921 was evaluated as a foliar application for the control of Botrytis bunch rot (Botrytis cinerea) in grape cv. Pinot Gris at Woodside, South Australia. AD-AU-1921 and Mirador® 625 were applied solo and in a tank mix and compared with the standard fungicide, Switch®.
Fungicides were applied five times as a foliar spray at BBCH 68, 71, 73, 79 and 81 using a motorised spray applicator in an application volume of 1200 to 1500 L/ha.
Assessment of Botrytis severity post-harvest indicated that AD-AU-1921 and Mirador® 625 applied together provided superior control to other treatments (Table 17). In fact, the mixture of AD-AU-1921 with Mirador® 625 exhibited synergy in control of botrytis bunch rot.
There were no visible signs of phytotoxicity or adverse growth effects in this trial.
Table 17. Efficacy of AD-AU-1921 on botrytis bunch rot (Botrytis cinerea) in grape cv. Pinot Gris. Woodside, South Australia
Figure imgf000025_0002
Bold indicates synergistic response (Colby) Field Trial 11
AD-AU-1921 was evaluated as a foliar application for the control of botrytis (Botrytis cinerea) in strawberry cv. Red Rhapsody at Wamuran, Queensland. AD-AU-1921 was applied solo and compared with Switch® and Solaris®. Fungicides were applied eight times as a foliar spray using a hand boom and an application volume of 800 L/ha. Fruit was harvested and incubated to encourage expression of disease symptoms.
Assessment of botrytis incidence indicated that AD-AU-1921 provided a similar reduction in Botrytis fruit infection (Table 18). The efficacy of Solaris® was generally poor, suggesting resistance was present at the trial site. AD-AU-1921 alone was able to provide similar control to Switch® and reduce the further exposure of this botrytis population to additional selection for anilinopyrimide resistance.
There were no visible signs of phytotoxicity or adverse growth effects in this trial.
Table 18. Efficacy of AD-AU-1921 on botrytis (Botrytis cinerea) in strawberry cv. Red Rhapsody. Wamuran, Queensland
Figure imgf000026_0001
DAA = days after application
Field Trial 12
AD-AU-1921 was evaluated for the control of grey mould (Botrytis cinerea) in grapevines cv. Marsanne at Stanthorpe, Queensland. Fungicides were applied at two timings: 80% capfall and berries 4 mm diameter. AD-AU-1921 was applied twice, in a tank mix with Solaris® at 80% capfall and solo at the second timing. Switch® at 80% capfall followed by Prolectus® was the comparative treatment. The sequence of AD-AU-1921 + Solaris® followed by AD-AU-1921 was the most effective treatment and provided complete control by the final assessment (Table 19).
There were no visible signs of phytotoxicity or adverse growth effects on either leaves or bunches by any treatment in this trial. Table 19. Efficacy of AD-AU-1921 on Botrytis in grapes. Stanthorpe, Queensland
Figure imgf000027_0001
1 Timings: A = 80% capfall; B = 4 mm berries.
DAA = days after application
Field Trial 13 AD-AU-1921 efficacy and synergy with Soprano® 500 was evaluated for the control of Septoria tritici blotch (Zymoseptoria tritici) in wheat cv. RGT Accroc at Gnarwarre, Victoria. Fungicides were applied as foliar sprays at two timings: BBCH 32 and 41. An assessment of Septoria tritici blotch infection and green leaf retention was undertaken at 28 days after the second application. The combination of AD-AU-1921 and Soprano® 500 was synergistic for STB control and increased the green leaf retention of older leaves such as the flag-3 (Table 20). Table 20. Efficacy of AD-AU-1921 on Septoria tritici blotch (STB) in wheat cv. RGT Accroc; 28 days after application two. Gnarwarre, Victoria
Figure imgf000028_0001
DAA = days after application Bold indicates synergistic response (Colby)
Field Trial 14
AD-AU-1921 efficacy and synergy with Proviso® was evaluated for the control of net type net blotch (Pyrenophora teres f.sp. teres) and spot type net blotch (Pyrenophora teres f.sp. maculata) in barley cv. Planet at Millicent, South Australia. Fungicides were applied as foliar sprays at two timings: BBCH 32 and 49. An assessment of net blotch infection was undertaken three days after the second application. Green leaf retention was assessed three and twenty days after the second application.
The combination of AD-AU-1921 and Proviso® was synergistic for net blotch control (Table 21) and increased the green leaf retention of older leaves such as the flag-2 and flag-3 (Table 22). Table 21. Efficacy of AD-AU-1921 on net blotches in barley cv. Planet. Millicent, South
Australia
Figure imgf000028_0002
STNB = spot type net blotch; NTNB = net type net blotch Bold indicates synergistic response (Colby)
Table 22. Green leaf retention in barley cv. cv. Planet. Millicent, South Australia
Figure imgf000029_0001
STNB = spot type net blotch; NTNB = net type net blotch
DAA = days after application
GLR = green leaf retention
Bold indicates synergistic response (Colby)
It will be appreciated that the formulation of the invention provides a new and useful addition to the industry, performing well in field trials, showing equivalence or superiority to other formulations or mixtures.
In particular, the effect of the formulation of the invention on control of Yellow Sigatoka (Mycosphaerella musicola). in bananas was beneficial, especially in view of the formulation's excellent crop safety
In relation to control of grey mould (Botrytis cinerea) in grapevines, the formulation of the invention proved very effective, performing as an equivalent to Switch, despite omitting cyprodinil (the other active in Switch®).
The new use as an in-furrow application in canola for the control blackleg (Leptosphaeria maculans) was unexpected, as was the synergistic effect when AD-AU-1921 was combined with flutriafol, azoxystrobin, epoxiconazole and prothioconazole. Industrial Applicability
The ability to apply solo fludioxonil and achieve good control of a range of disease offers end users the ability to use fludioxonil in rotation with other fungicide modes of action or in alternative tank mixtures and help manage fungicide resistance risk. Use of fludioxonil as in in-furrow application as described is also beneficial, as are the synergistic combinations disclosed.

Claims

Claims
1. A stable, highly loaded fludioxonil suspension concentration formulation with more than 250 g a i/L of fludioxonil.
2. The formulation of claim 1, which includes about 500 g a i/L of fludioxonil.
3. The formulation of claim 1 or 2, which includes one or more of a dispersant, a wetting agent, a stabiliser, a humectant, a rheology modifier, a preservative and an anti-foaming agent.
4. The formulation of claim 3, wherein the ratio of fludioxonil to total raw material (other than water) is equal to or more than about 5:1.
5. The formulation of any one of claims 1 to 4, which has an aqueous content of, or less than, 60% w/v.
6. The formulation of any one of claims 1 to 5 when used in combination or in a sequence with at least one additional fungicide chosen from de-methylation inhibitor fungicides, phthalimide fungicides and strobilurin fungicides.
7. The formulation of claim 6, wherein the at least one additional fungicide is chosen from flutriafol, azoxystrobin, epoxiconazole and prothioconazole.
8. The formulation of any one of claims 1 to 5 wherein fludioxonil is the sole active.
9. A synergistic fungicidal mixture comprising fludioxonil and at least one additional fungicide, plant activator or fertiliser.
10. The synergistic fungicidal mixture as claimed in claim 9, wherein the at least one additional fungicide is chosen from de-methylation inhibitor fungicides, phthalimide fungicides and strobilurin fungicides.
11. The synergistic fungicidal mixture as claimed in claim 9 or 10, wherein the at least one additional fungicide is chosen from flutriafol, azoxystrobin, epoxiconazole and prothioconazole.
12. A method for controlling a fungal disease, including the steps of: as a first step in a sequence, applying a composition containing fludioxonil as an active ingredient, as well as a composition containing as an active ingredient a fungicide having a mode of action different from that of fludioxonil, to a crop or ground area intended for growing a crop; and as a last step in the sequence, applying to the crop or ground area intended for growing the crop a composition containing fludioxonil as an active ingredient without any a fungicide having a mode of action different from that of fludioxonil. The method of claim 12, which includes a second step of applying a composition containing as an active ingredient a fungicide having a mode of action different from that of fludioxonil, but without fludioxonil, the second step preceding the last step. The method of claim 12 or 13, wherein for the first step fludioxonil is either tank mixed or coformulated with the other mode of action fungicide or each fungicide is applied separately. The method of any one of claims 12 to 14, wherein the other mode of action fungicide is chosen from de-methylation inhibitor fungicides, phthalimide fungicides and strobilurin fungicides. The method of any one of claims 12 to 15, wherein the other mode of action fungicide is chosen from flutriafol, azoxystrobin, epoxiconazole and prothioconazole. A method of controlling a fungal pathogen comprising applying to a locus of the pathogen a fungicidally effective amount of the formulation claimed in any one of claims 1 to 8 or the mixture claimed in any one of claims 9 to 11. The method of claim 17, wherein the locus of the pathogen is chosen from one or more of cereals, wheat, winter wheat, spring wheat, barley, winter barley, spring barley, triticale, cereal rye, fodder cereals, rice, canola, oilseed rape, maize, cotton, bananas, grapevines, pome fruit, stone fruit, almonds, macadamias, mangoes, strawberries and other berry crops, coffee, chickpeas, green beans, lettuce, leafy vegetables, potatoes, Allium spp, field peas, lentils, lupins, peanuts, soybeans, sugarcane, sugarbeet, fodder beet, beet vegetables, sunflower, non-crop areas, turfgrass and grassland. The method of claim 17 or 18, wherein the pathogen is one or more of Botrytis spp,
Sclerotinia spp, Alternaria spp, Mycosphaerella spp, Cercospora spp, Fusarium spp, Rhizoctonia spp, Zymoseptoria tritici, Rhizopus spp, Phakopsora pachyrhizi, Pyrenophora spp, Monilinia spp, Colletotrichum spp, Penicillium spp, Aspergillus spp and Puccinia spp. A method of controlling blackleg (Leptosphaeria maculans) in canola, which includes applying in-furrow a synergistic combination of the fludioxonil formulation claimed in any one of claims 1 to 7 with flutriafol.
PCT/AU2022/051043 2021-08-25 2022-08-25 Highly loaded fludioxonil formulations WO2023023815A1 (en)

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